4-Methylmorpholine → N,N'-Dicyclohexylurea

HRID 617112

Reaktionsgleichung

Reaktionsgleichung von HRID 617112
[CH2-]C(C)=[O:3].CN1CCOCC1.ON1C2C=CC=CC=2N=N1.[CH2:22]1[CH2:27][CH2:26][CH:25]([N:28]=[C:29]=[N:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)[CH2:24][CH2:23]1>CC(C)=O.C1COCC1>[C:29]([NH:28][CH:25]1[CH2:24][CH2:23][CH2:22][CH2:27][CH2:26]1)([NH:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)=[O:3]

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 178477758HCID 178477758, Verbindung

Produkt 1

HCID 4277N,N'-Dicyclohexylurea

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of freshly prepared acetonide-protected amino acid (0.2 mmol, 1 equiv) in acetone (1.5 mL) was added 3 mL of THF, N-methylmorpholine (0.22 mmol, 1.1 equiv), 1-hydroxybenzotriazole (0.44 mmol, 2.2 equiv), and hexapeptide amine (0.22 mmol, 1.1 equiv). The resultant mixture was cooled to 0° C. and DCC (0.22 mmol, 1.1 equiv) was added. The mixture was allowed to warm up to room temperature and stirred under N2 for 20 h, after which time the precipitated dicyclohexylurea (DCU) was removed by filtration and washed with small portion of CH2Cl2. The combined filtrate was washed with saturated NaHCO3 solution and dried over MgSO4. Concentration in vacuo and dissolution of the residue in EtOAc yielded more DCU. The residue remaining after a second filtration and concentration in vacuo was purified by chromatography with 10-40% acetone in freshly distilled n-hexane to give the N,O-Isopropylidene-protected heptapeptide 1-7 (SEQ ID NO:10).

Aufarbeitung

  1. customafter which time the precipitated dicyclohexylurea (DCU) was removed by filtration
  2. washwashed with small portion of CH2Cl2
  3. washThe combined filtrate was washed with saturated NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. concentrationConcentration
  6. dissolutionin vacuo and dissolution of the residue in EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-b99bcbe6cc764619a6512372c8babae6
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05948693

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